Asymmetric Gold-Catalyzed Hydroarylation/Cyclization Reactions

被引：133

作者：

Chao, Chung-Meng ^{[1
]}

Vitale, Maxime R. ^{[1
]}

Toullec, Patrick Y. ^{[1
]}

Genet, Jean-Pierre ^{[1
]}

Michelet, Veronique ^{[1
]}

机构：

[1] Ecole Natl Super Chim Paris, UMR 7573, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 06期

关键词：

asymmetric catalysis; cyclization; electron-rich arenes; gold; tandem reaction; INTRAMOLECULAR HYDROAMINATION; C-C; CYCLOISOMERIZATION; ENYNES; EFFICIENT; ALKOXYCYCLIZATION; CYCLIZATION; HYDROXYCYCLIZATION; HETEROCYCLES; CARBOCYCLES;

D O I：

10.1002/chem.200802341

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric gold-catalyzed hydroarylation/cyclization reactions of 1,6-enynes under mild conditions was investigated. A mixture of L-(AuCl) 2 (L=(R)-MeO-BIPHEP or (R)-4-MeO-3,5-(tBu)2MeOBIPHEP) (3 mol %) and AgOTf (6 mol %) in distilled Et2O was stirred under argon atmosphere at room temperature for 30 minutes. The aromatic nucleophile was then added and the mixture was stirred for 5 minutes. Enyne was finally added and the mixture was stirred until completion of the reaction. The mixture was then filtered through a short pad of silica to eliminate the catalyst and the solvents were evaporated under reduced pressure. the crude product was purified by silica gel flash chromatography. It was observed that the combination of atropisomeric electron-rich and hindered chiral ligand 4-MeO-3,5-(tBu) 2MeOBIPHEP associated to Au1 and silver salt promotes the enantioselective hydroarylation/cyclization reaction of 1,6-enynes.

引用

页码：1319 / 1323

页数：5

共 99 条

[71] Gold(I)-catalyzed cyclizations of 1,6-enynes:: Alkoxycyclizations and exo/endo skeletal rearrangements [J].